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Oxygen‐substituted isocyanates (O‐isocyanates) are rare isocyanates with a reported propensity to trimerize, a side‐reaction that severely limited their use in synthesis. Herein, the development of blocked (masked) O‐isocyanate precursors that form this reactive intermediate in situ provide controlled reactivity, allowing the first examples of cascade reactions involving O‐isocyanates. Complex hydroxylamine‐derived hydantoins and dihydrouracil compounds can be rapidly assembled from α‐ and β‐amino esters, illustrating the convenience of masked O‐isocyanates as hydroxylamine derived building blocks. Evidence for the intermediacy of an O‐isocyanate intermediate is provided.